Sodium Bicarbonate → Oritavancin

HRID 1397115Notes

Reaction equation

HRID 1397115 reaction equation
[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@@H:100]3[NH:101][C:102](=[O:103])[C@@H:81]([C:82]4[CH:83]=[CH:84][C:85]([OH:107])=[C:86]([C:88]5[C:93]([OH:94])=[CH:92][C:91]([OH:95])=[CH:90][C:89]=5[C@@H:96]([C:104]([OH:106])=[O:105])[NH:97][C:98]3=[O:99])[CH:87]=4)[NH:80][C:78](=[O:79])[C@H:77]3[C:20]4=[CH:21][C:22]([O:60][C:61]5[CH:62]=[CH:63][C:64]([C@@H:68]([OH:122])[C@@H:69]([NH:112][C:113]([C@H:115]([NH:120][CH3:121])[CH2:116][CH:117]([CH3:119])[CH3:118])=[O:114])[C:70]([NH:72][C@@H:73]([CH2:108][C:109]([NH2:111])=[O:110])[C:74]([NH:76]3)=[O:75])=[O:71])=[CH:65][C:66]=5[Cl:67])=[C:23]([O:24][C@@H:25]3[O:30][C@H:29]([CH2:31][OH:32])[C@@H:28]([OH:33])[C@H:27]([OH:34])[C@H:26]3[O:35][C@@H:36]3[O:41][C@@H:40]([CH3:42])[C@H:39]([OH:43])[C@:38]([NH:45][CH2:46][C:47]5[CH:48]=[CH:49][C:50]([C:53]6[CH:54]=[CH:55][C:56]([Cl:59])=[CH:57][CH:58]=6)=[CH:51][CH:52]=5)([CH3:44])[CH2:37]3)[C:18](=[CH:19]4)[O:17][C:13]3=[C:14]([Cl:16])[CH:15]=[C:10]2[CH:11]=[CH:12]3)[CH2:5][C@@:4]([NH2:124])([CH3:123])[C@H:3]1[OH:125].OP(O)(O)=O.C([O-])(O)=O.[Na+].C(=O)([O-])ON1C(=O)CCC1=O>O1CCOCC1.O>[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@@H:100]3[NH:101][C:102](=[O:103])[C@@H:81]([C:82]4[CH:83]=[CH:84][C:85]([OH:107])=[C:86]([C:88]5[C:93]([OH:94])=[CH:92][C:91]([OH:95])=[CH:90][C:89]=5[C@@H:96]([C:104]([OH:106])=[O:105])[NH:97][C:98]3=[O:99])[CH:87]=4)[NH:80][C:78](=[O:79])[C@H:77]3[C:20]4=[CH:21][C:22]([O:60][C:61]5[CH:62]=[CH:63][C:64]([C@@H:68]([OH:122])[C@@H:69]([NH:112][C:113]([C@H:115]([NH:120][CH3:121])[CH2:116][CH:117]([CH3:118])[CH3:119])=[O:114])[C:70]([NH:72][C@@H:73]([CH2:108][C:109]([NH2:111])=[O:110])[C:74]([NH:76]3)=[O:75])=[O:71])=[CH:65][C:66]=5[Cl:67])=[C:23]([O:24][C@@H:25]3[O:30][C@H:29]([CH2:31][OH:32])[C@@H:28]([OH:33])[C@H:27]([OH:34])[C@H:26]3[O:35][C@@H:36]3[O:41][C@@H:40]([CH3:42])[C@H:39]([OH:43])[C@:38]([NH:45][CH2:46][C:47]5[CH:52]=[CH:51][C:50]([C:53]6[CH:58]=[CH:57][C:56]([Cl:59])=[CH:55][CH:54]=6)=[CH:49][CH:48]=5)([CH3:44])[CH2:37]3)[C:18](=[CH:19]4)[O:17][C:13]3=[C:14]([Cl:16])[CH:15]=[C:10]2[CH:11]=[CH:12]3)[CH2:5][C@@:4]([NH2:124])([CH3:123])[C@H:3]1[OH:125]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 22239412(2,5-Dioxopyrrolidin-1-yl) carbonateHCID 70691404171099-57-3(Free base)

Product 1

HCID 16136912Oritavancin

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To oritavancin bisphosphoric acid salt (5, 180 mg, 0.0905 mmol) in 1,4-dioxane (2 mL) and H2O (2 mL) was added NaHCO3 (25 mg, 0.29 mmol) and the mixture was stirred until all of 5 had dissolved. A solution of 34 (135 mg, 0.164 mmol) in 1,4-dioxane (3 mL) was added and the resulting solution was stirred at room temperature overnight. The product was precipitated by the addition of H2O and collected by filtration. The crude product was purified by C18 reversed phase chromatography on a Biotage™ flash chromatography system (30% to 80% MeCN in 0.2% TEA/phosphate pH 3) to give 37 (135 mg, 55%, based on the di-phosphoric acid salt) as a white solid: ESI-MS (M+2H) calculated for C120H157Cl3N14O38 1256.0. found 1255.4

Workup

  1. dissolutionhad dissolved
  2. stirringthe resulting solution was stirred at room temperature overnight
  3. customThe product was precipitated by the addition of H2O
  4. filtrationcollected by filtration
  5. customThe crude product was purified by C18 reversed phase chromatography on a Biotage™ flash chromatography system (30% to 80% MeCN in 0.2% TEA/phosphate pH 3)

Sources & evidence

ORD record
ord-115589a5fbe34b64b5e6aa30290383dc
Source dataset
uspto-grants-2014_12
Patent number
US08901072B2

Reaction notes

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